Aromatic Mannich compound-containing composition and process for making same

Abstract

This invention relates to a composition, comprising: (I) an aromatic Mannich compound derived from: (A) a hydroxy containing aromatic compound having the formula  wherein in Formula (A-1): Ar is an aromatic group; m is 1, 2 or 3; n is a number from 1 to about 4; with the proviso that the sum of m and n does not exceed the number of available positions on Ar that can be substituted; each R 1 independently is a hydrocarbyl group of up to about 400 carbon atoms; and R 2 is H, amino or carboxyl; (B) an aldehyde or ketone having the formula  or a precursor thereof; wherein in Formula (B-1): R 1 and R 2 independently are H or hydrocarbyl groups having from 1 to about 18 carbon atoms; and R 2 can also be a carbonyl-containing hydrocarbyl group having from 1 to about 18 carbon atoms; and (C) a mixture of water and an amine, said amine containing at least one primary or secondary amino group; and (II) alcohol. The invention also relates to a process for making the foregoing composition.

What is claimed is:  
     
       1. A composition, comprising 
       (I) an aromatic Mannich compound derived from:  
       (A) a hydroxy containing aromatic compound having the formula                    
        wherein in Formula (A-1): Ar is an aromatic group; m is 1, 2 or 3; n is a number from 1 to about 4; with the proviso that the sum of m and n does not exceed the number of available positions on Ar that can be substituted; each R 1  independently is a hydrocarbyl group of up to about 400 carbon atoms; and R 2  is H, amino or carboxyl;  
       (B) an aldehyde or ketone having the formula                    
        or a precursor thereof; wherein in Formula (B-1): R 1  and R 2  independently are H or hydrocarbyl groups having from 1 to about 18 carbon atoms; and R 2  can also be a carbonyl-containing hydrocarbyl group having from 1 to about 18 carbon atoms; and  
       (C) a mixture of water and an amine, said amine containing at least one primary or secondary amino group; and  
       (II) alcohol.  
     
     
       2. The composition of claim  1  wherein in Formula (A-1), Ar is a benzene nucleus, R 2  is H, n is 1, and m is 1. 
     
     
       3. The composition of claim  1  wherein in Formula (A-1), R 1  is an alkyl, alkenyl or cycloalkyl group. 
     
     
       4. The composition of claim  1  wherein in Formula (A-1), R 1  is a hydrocarbyl group derived from an olefin polymer. 
     
     
       5. The composition of claim  1  wherein in Formula (A-1), R 1  is a polyolefin group, said polyolefin group being derived from ethylene; propylene, butene-1; butene-2; isobutene; pentene-1; hexene-1; heptene-1; octene-1; nonene-1; decene-1; pentene-2; or a mixture of two or more thereof. 
     
     
       6. The composition of claim  1  wherein in Formula (A-1), R 1  is a polyisobutene group. 
     
     
       7. The composition of claim  1  wherein in Formula (A-1), R 1  is a polyisobutene group made by the polymerization of a C 4  refinery stream having a butene content of about 35 to about 75% by weight and an isobutene content of about 30 to about 60% by weight. 
     
     
       8. The composition of claim  1  wherein in Formula (A-1), R 1  is derived from a polyisobutene having a methylvinylidene isomer content of at least about 70%. 
     
     
       9. The composition of claim  1  wherein in Formula (A-1), R 1  is a polyisobutene group having a number average molecular weight of about 300 to about 5000. 
     
     
       10. The composition of claim  1  wherein in Formula (B-1), R 1  and R 2  are independently H or hydrocarbyl groups of 1 to about 6 carbon atoms. 
     
     
       11. The composition of claim  1  wherein (B) is formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde, benzaldehyde, acetone, methyl ethyl ketone, ethyl propyl ketone, butyl methyl ketone, glyoxal or glyoxylic acid. 
     
     
       12. The composition of claim  1  wherein said pecursor of said aldehyde or ketone is paraformaldeyde, formalin or trioxane. 
     
     
       13. The composition of claim  1  wherein (B) is paraformaldehyde. 
     
     
       14. The composition of claim  1  wherein said amine is a compound represented by the formula                    
       wherein in Formula (C-1), R 1  and R 2  are independently hydrogen, hydrocarbyl groups, amino-substituted hydrocarbyl groups, hydroxy-substituted hydrocarbyl groups, or alkoxy-substituted hydrocarbyl groups. 
     
     
       15. The composition of claim  1  wherein said amine is ammonia; methylamine; dimethylamine; N-methyl-ethyl-amine; N-methyloctylamine; N-cyclohexyl-amine; dibutylamine; cyclohexylamine; aniline; dodecylamine; octadecylamine; o-phenylene-diamine; N,N′-di-n-butyl-p-phenylenediamine; morpholine; piperazine; tetrahydropyrazine; indole; hexahydro-1,3,5-triazine; 1-H-1,2,4-triazole; melamine; bis-(p-aminophenyl)methane; phenyl-methylenimine; menthanediamine; cyclohexylamine; pyrrolidine; 3-amino-5,6-diphenyl-1,2,4-triazine; ethanolamine; diethanolamine; quinonediimine; 1,3-indandiimine; 2-octadecylimidazoline; 2-phenyl-4-methyl-imidazolidine; oxazolidine; 2-heptyl-oxazolidine; or a mixture of two or more thereof. 
     
     
       16. The composition of claim  1  wherein said amine is a hydroxyl-containing amine represented by the formula                    
       wherein in Formula (C-2): each of R 1 , R 3  and R 4  independently is H or a hydrocarbyl, hydroxyhydrocarbyl, aminohydrocarbyl, or hydroxyaminohydrocarbyl group provided that at least one of R 3  is a hydroxyhydrocarbyl or a hydroxy-aminohydrocarbyl group; R 2  is an alkylene group; and n is a number in the range of zero to about 5. 
     
     
       17. The composition of claim  1  wherein said amine is ethanolamine; 2-amino-1-butanol; 2-amino-2-methyl-1-propanol; di-(3-hydroxypropyl)amine; 3-hydroxybutyl-amine; 4-hydroxybutyl-amine; 2-amino-1-butanol; 2-amino-2-methyl-1-propanol; 2-amino-1-propanol; 3-amino-2-methyl-1-propanol; 3-amino-1-propanol; 2-amino-2-methyl-1,3-propanediol; 2-amino-2-ethyl-1,3-propanediol; diethanolamine; di-(2-hydroxypropyl)amine; N-(hydroxypropyl)-propylamine; N-(2-hydroxyethyl)-cyclohexylamine; 3-hydroxycyclopentylamine; N-hydroxyethyl piperazine; or a mixture of two or more thereof. 
     
     
       18. The composition of claim  1  wherein said amine is a polyamine represented by the formula                    
       wherein in Formula (C-3): n is a number in the range of 1 to about 10; R 1  and R 2  are independently H or hydrocarbyl groups of 1 to about 30 carbon atoms; and R 3  is an alkylene group of 1 to about 10 carbon atoms. 
     
     
       19. The composition of claim  1  wherein said amine is ethylene diamine; triethylene tetramine; propylene diamine; decamethylene diamine; octamethylene diamine; di(heptamethylene)triamine; tripropylene tetramine; tetraethylene pentamine; trimethylene diamine; pentaethylene hexamine; di(trimethylene)-triamine; 2-heptyl-3-(2-aminopropyl)imidazoline; 4-methyl-imidazoline; 1,3-bis(2-aminoethyl)imidazoline; pyrimidine; 1-(2-aminopropyl)piperazine; 1,4-bis(2-aminoethyl)piperazine; 2-methyl-1-(2-amino-butyl)piperzine; or a mixture of two or more thereof. 
     
     
       20. The composition of claim  1  wherein said amine is ethylene diamine. 
     
     
       21. The composition of claim  1  wherein said alcohol is a fuel soluble hydrocarbon-based alcohol containing up to about 20 aliphatic carbon atoms. 
     
     
       22. The composition of claim  1  wherein said alcohol is methanol; ethanol; n-propanol; isopropanol; n-butanol; isobutanol; sec-butanol; tert-butanol; 3-methyl-1-butanol; n-pentanol; isopentanol; amyl alcohol; iso-amyl alcohol; cyclopentanol; n-hexanol; cyclohexanol; 2-methyl-4-pentanol; heptanol; octanol; 2-ethyl hexanol; decanol; dodecanol; tetradecanol; hexdecanol; octadecanol; allyl alcohol; crotyl alcohol; methyl vinyl carbinol; or a mixture of two or more thereof. 
     
     
       23. The composition of claim  1  wherein said alcohol is 2-ethyl hexanol. 
     
     
       24. The composition of claim  1  wherein the equivalent ratio of (A):(B):(C) is about 1:(1 to 2):(0.5 to 2). 
     
     
       25. The composition of claim  1  wherein the weight ratio of said amine to said water is from about 50:50 to about 99:1. 
     
     
       26. The composition of claim  1  wherein the weight ratio of said aromatic Mannich compound (I) to said alcohol (II) is from about 85:15 to about 10:90. 
     
     
       27. A composition, comprising: 
       (I) an aromatic Mannich compound derived from: (A) a polyiso-butene-substituted phenol wherein the polyisobutene substituent is derived from a polyisobutene having a methylvinylidene isomer content of at least about 70%; (B) paraformaldehyde; and (C) a mixture of water and ethylene diamine; and  
       (II) 2-ethyl hexanol.  
     
     
       28. A fuel composition comprising a major amount of a normally liquid hydrocarbon fuel, and a minor amount of the composition of claim  1 . 
     
     
       29. A process, comprising: 
       reacting (A) a hydroxy containing aromatic compound having the formula                    
        wherein in Formula (A-1): Ar is an aromatic group; m is 1, 2 or 3; n is a number from 1 to about 4; with the proviso that the sum of m and n does not exceed the number of available positions on Ar that can be substituted; each R 1  independently is H or a hydrocarbyl group having from 1 to about 400 carbon atoms; and R 2  is H, amino or carboxyl;  
       with (B) an aldehyde or ketone having the formula                    
        or a precursor thereof; wherein in Formula (B-1): R 1  and R 2  independently are H or hydrocarbyl groups having from 1 to about 18 carbon atoms; and R 2  can also be a carbonyl-containing hydrocarbyl group having from 1 to about 1 8 carbon atoms; and  
       and (C) a mixture of water and an amine, said amine containing at least one primary or secondary amino group;  
       in the presence of alcohol.  
     
     
       30. The process of claim  29  wherein the equivalent ratio of (A):(B):(C) is about 1:(1 to 2):(0.5 to 2). 
     
     
       31. The process of claim  29  wherein the weight ratio of said amine to said water is from about 50:50 to about 99:1. 
     
     
       32. The process of claim  29  wherein the weight ratio of the reaction product of (A), (B) and (C) to said alcohol is from about 85:15 to about 10:90. 
     
     
       33. The process is of claim  29  wherein said process is conducted at a temperature of about 40 to about 200° C. 
     
     
       34. A process for making an aromatic Mannich compound, comprising: 
       reacting (A) a polyisobutene-substituted phenol wherein the polyisobutene substituent is derived from a polyisobutene having a methylvinylidene isomer content of at least about 70%; with (B) paraformaldehyde; and (C) a mixture of water and ethylene diamine;  
       in the presence of 2-ethyl hexanol.